


A FIRST TIME THAT COUNTS

by Slytherin_your_dms



Category: Teen Wolf (TV)
Genre: Bisexual Stiles Stilinski, Bottom Derek Hale, Bottom Derek Hale/Top Stiles Stilinski, Derek Hale & Erica Reyes Friendship, Dirty Talk, First Time, Gay Derek Hale, Love Confessions, M/M, Mentioned Jennifer Blake, Mentioned Kate Argent, Praise Kink, Stiles Stilinski Has a Big Dick, Stiles Stilinski is Not a Virgin, Tooth-Rotting Fluff, Trust, Virgin Derek Hale
Language: English
Status: Completed
Published: 2020-08-09
Updated: 2020-08-09
Packaged: 2021-03-05 22:48:33
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,936
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/25583125
Author URL: https://archiveofourown.org/users/Slytherin_your_dms/pseuds/Slytherin_your_dms
Summary: Derek is a virgin, he doesn't count his past relationships. After countless tries, he confides in Erica who tells him to go to someone he can trust. That person just so happens to be Stiles, who is more than willing to help Derek out, and possibly more.
Relationships: Derek Hale/Original Male Character(s), Derek Hale/Stiles Stilinski
Kudos: 79





	A FIRST TIME THAT COUNTS

**Author's Note:**

> enjoy!! also, bottom derek is hot.

Derek was a virgin, not really, but in his mind. He’d only had sex with Kate, Jennifer and Braeden but well Kate was a psycho, Jennifer was an actual monster and Braeden sucked his dick once then left forever. So, Derek didn't count any of these as first times plus, now he had finally come out as gay, (Peter and Cora were not surprised at all) he could lose his virginity to a guy, someone willing to fuck him, someone he can trust. He decided to regularly visit the jungle and get grindr, he was basically desperate, and didn't want anyone who was a complete creep. First, it was Chad, a 23 year old frat boy, you can probably tell how that ended. Then, Robbie, him and Derek went out for a week before Derek walked in on Robbie, who claimed he was gay, balls deep in Brittany. Next, Samuel, after two whole months of dates and make out sessions, Derek was ready. The pair had gotten so close, as in Derek had two of the dude's fingers in his ass, that's when Robbie started dirty talking, it started off hot, Derek was into it. Then Robbie started talking about how he wanted to see Derek bleeding, and it just got creepier. Derek ran to the bathroom saying he had to pee real quick and made Erica fake an emergency to help him get the fuck out of there. Finally, Calum, the pair had met at the jungle and Derek decided fuck it, he would just go home with this guy. They had got halfway to the loft when Parrish pulled them over, Calum was actually John, a drug lord on the run all the way from Texas, so that backfired. Derek was sick of his bad luck. So, he went to Erica.  
"Look Der, you need to go to someone you already know, already trust, meeting guys at bars or online isn't working out so do it the old fashioned way." "Erica, 1) I don’t know any guys who are interested in guys that would be willing to do that and 2) the guy I'm totally in love with would just laugh and tell everyone about how pathetic I am-" "Wait Der, you love someone? and you know and trust him?" "Yes Er I love him, I really fucking do, he doesn't like me back, we kissed at a party last year and he ran away, that's why I decided to pity fuck that Calum dude, and even that didn't go to plan." "Stiles" Derek blushed, of course she knew, of fucking course, "Yeah, I'm in love with Stiles, head over heels." "WHAT?! I was saying you should go to Stiles, oh my god you love him too!" "TOO what do you mean too?!" "Derek, the dude has loved you for 4 years, go get your guy!"  
Derek practically sprints out of the downtown apartment scrambling with his keys to start the camaro to rush to Stiles' place. The limit is 45 but he is going 60, he needs to get to Stiles' right now. When he reaches the house, he sees the light on upstairs but not in the hall so for old times sake he scaled the wall and knelt on the ledge outside the window. He tapped on the glass and waited, those 12 seconds were the longest 12 seconds of his life. When the window opened, he wasted no time and pounced on Stiles, attaching their lips harshly. He pulled away after a moment to breathe, “Der, what are you doing here-“ “I love you too ok, I love you too and I came here because I trust you and I want you, no, no Stiles I NEED you! You’re my mate and I can’t hold this off anymore Stiles I, we need you!” The only reply Derek got was when Stiles grabbed him by the back of the neck and smashed their lips together again, licking at the taller man’s lips, Stiles managed to gain access to Dereks mouth. He explored every part of it making their tongues dance together. The kiss was wet, sloppy and downright sinful. Derek grabbed at the hem of Stiles’ shirt and tore it off, moaning at the sight of Stiles’ bare chest covered in moles. His nipples hard and a trail of dark hair disappearing into his sweatpants. Stiles moved down to Derek’s jaw, nipping and sucking as if his life depended on it. His slender, nimble fingers unbuttoned Derek’s shorts and pushed them past his bubble butt. ”You look so fucking hot in those shorts, I have to restrain myself from bending you over and fucking you every time you wear them.” Derek whined, a high pitch noise that came from deep within his throat. “Too many clothes, Sti take them off, all off” Stiles complies, yanking down his pants and then undressing Derek, before softly laying him on the bed. The mood had changed, Stiles knew they were in no rush, the once frantic atmosphere was calmer yet just as erotic. Stiles crawls up the bed to Derek’s feet and smiles sweetly, “Der baby, can you spread your legs for me?” Derek is anxious, he feels weird exposing his most private place but he trusts Stiles, he knows him, “O-ok” He lets his legs fall open, revealing his leaking cock and his tight little hole to the man he loves, “So good for me, my good mate trusting me, so brave.” Derek blushes at the praise he receives and barely notices Stiles reaching in front of him for the lube. “Baby, I’m gonna prep you now, get you nice and ready for my cock ok?” Derek nods, biting his lip in anticipation, Stiles moves in between his legs and presses his lips to his mates once again, this time it’s soft and slow. He circles a finger around Derek’s rim, waiting for him to relax, “My gorgeous boy, it’s ok, relax I’ve got you, I’m right here.” Derek groans into Stiles mouth and instantly releases any tension he held, he wants this, not only for him, but he has the need to please his mate. Stiles’ finger slips past the ring of muscle, eliciting another whimper from the man underneath him.  
After thrusting his middle finger in and out, he adds another, Derek writhes on the bed, his mouth in a permanent silent ‘o’ shape, “Sti, baby I’m gonna- I can’t-“ “Let go Der, it’s ok you can let go..” He is cut of by a high pitched moan. Derek’s hips thrust up, his cock twitching and releasing spurts of thick cum, his very first untouched orgasm. “So good for me, one day I want you to fill me with this alpha seed and breed me, make me yours.” Somehow, Derek’s cock still stands proudly at 7.5 inches, hard and red. Stiles is now driving three fingers inside of Derek and manages to squeeze in his pinky to make sure his lover is comfortable. Derek grasps Stiles hair, pulling him to his chest and Stiles takes the opportunity to suck at his nipples, making them hard and sensitive, nipping one before moving to the other, it only takes two more minutes before Derek is grinding back onto Stiles’ hand, “Sti, please, fuck me!” he manages to gasp out. “No,” Derek gets scared, “I’m not fucking you, I’m making love to you baby, gonna show you how thankful I am that you’re mine and I’m yours, gonna take care of my amazing, strong alpha!” Derek can feel his wolf preening at the acceptance of the mating bond, he lets him come to the surface, his eyes shining blue, “So beautiful Der, you ready?” Derek nods and watches as Stiles coats his member in lube, it’s cut, longer than his own and thick like a beer can Derek moans at the fact that it’s going to be inside of him. Stiles swoops down and captures Derek’s lips and pushes the tip of his cock at Derek’s entrance. He brackets Derek’s head with his arms and plants his knees so he will be able to thrust his hips. When the head of his cock passes the initial muscle, the pair moan loudly, Stiles is overwhelmed by the feeling of Derek’s tight ass around him and Derek by the feeling of his mates thick cock inside of him. Stiles ever so slowly pushes forward, filling Derek’s virgin hole little by little. “So tight baby, fuck!” Derek whimpers at the fact he is pleasing his mate. “Stiles, oh my god you feel so good, filling me up!”  
Stiles grunts when he is fully sheathed, waiting so he doesn’t cum prematurely. Derek clearly gets impatient as his eyes flash blue and he rolls his hips making the pair groan. Stiles' thrusts start out shallow, his length grazing his lovers tight walls. As He continues these thrusts, Derek can't help but think, he wouldn't let anyone but Stiles control him, he is submitting to the lithe man in a way he has been scared to do since he was 23, he trusts Stiles, and wants this to be his forever, his home. "I want that too Der, I'm so happy to be here with you, in this position, I'll always be here." Derek whines, a mixture of embarrassment at the realisation that he said that all out loud but also at the fact that Stiles finishes every word with a sharp jolt of his hips. The sound of Stiles' heavy balls slapping against Derek's ass fill the room, every thrust is filled with pure adoration. "Please baby, please harder!!" Stiles drives his hips deeper into Derek as he sucks and bites at the werewolf's bottom lip, there is sweat dripping down his chin and landing on Derek's neck, which should disgust him, but it makes the room smell so good, elements of sex, arousal and just Stiles, his scent of vanilla, cinnamon and oranges fills Derek's nostrils and makes a heat bubble in his lower abdomen. The place is maddening for Stiles but he continues to jackrabbit into Derek until he is spasming around him. Derek's back arches, his toes curl, his eyes roll back with his second orgasm of the night, his ass clenches around Stiles making him feel impossibly full, jaw locking on Stiles' collar bone, breaking his skin to form a mating bite. Derek claims the younger man as his own, forever. He practically howls when after three brutal jerks of his pelvis, Stiles shoots cum deep inside him screaming his name, "Shit.. DEREK OH FUCK!!!!" The older man can feel his mate's cock twitching inside of him as they bask in their afterglows, both of them wincing at the feeling of Stiles' soft cock slipping out of Derek's abused hole. Then Derek blacks out.  
He awakes in Stiles' bed, alone and wearing a pair of grey sweatpants, at first he is scared that Stiles has left him, but he listens for his newly claimed mate's heartbeat and follows it downstairs. His ass burns deliciously and every wobbly step he takes, reminds him of last night's events. He trudges into the kitchen to see Stiles in a baggy t-shirt and boxers with his bite mark on show, pouring coffee into two mugs on the counter, "Morning sleepy head." Stiles passes Derek his coffee and snuggles into his side. "I thought you left me.." Stiles makes Derek put the cup down and jumps into his arms, connecting their lips chastely, "I meant it when i said forever sourwolf." Derek licks over the bite, "home.. mine." "Yours.”

**Author's Note:**

> fic dedicated to amber who is going to top and whip derek hale one day :)  
> (feel free to request ideas in the comments)


End file.
